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Extra Crunch roundup: Metromile CEO interview, Oscar Health’s IPO plans, our 2-year anniversary, more

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Image Credits: Andrii Lysenko (opens in a new window) / Getty Images

I’m very proud of the work we’re doing here at Extra Crunch, so it gives me great pleasure to announce that today is our second anniversary.

Thanks to hard work from the entire TechCrunch team, authoritative guest contributors and a very engaged reader base, we’ve tripled our membership in the last 12 months.

As Extra Crunch enters its third year, we’re putting our foot on the gas in 2021 so we can bring you more:


Full Extra Crunch articles are only available to members
Use discount code ECFriday to save 20% off a one- or two-year subscription


To be completely honest: Eric and I wavered about posting this announcement. Both of us would prefer to show the results of our work than make a list of future-looking statements, so I’ll sum up:

I’m proud of the work we’re doing because people around the world use the information they find on Extra Crunch to build and grow companies. That’s big!

Thanks very much for reading Extra Crunch; have a great weekend.

Walter Thompson
Senior Editor, TechCrunch
@yourprotagonist

Extra Crunch turns two second anniversary image: a cake with two candles and the EC logo
Image Credits: Bryce Durbin

2 years in, Extra Crunch is helping readers build and grow companies around the world

Will ride-hailing profits ever come?

Image Credits: Nigel Sussman (opens in a new window)

Before the pandemic began, I took about seven or eight hailed rides each month. Since I began physically distancing from others to stem the spread of the coronavirus in March 2020, I’ve taken exactly 10 hailed rides.

Your mileage may vary, but last year, Uber and Lyft both reported steep revenue losses as travelers hunkered down at home. Today, Alex Wilhelm says both transportation platforms plan to reach adjusted profitability by Q4 2021.

He unpacked the numbers “to see if what the two companies are dangling in front of investors is worth desiring.” Since he usually doesn’t focus on publicly traded stocks, I asked Alex why he focused on Uber and Lyft today.

“Utter confusion,” he replied.

“Investors have bid up their stocks like the two companies are crushing the game, instead of playing a game with their numbers to reach some sort of profit in the future,” Alex explained. “The stock market makes no sense, but this is one of the weirder things.”

Will ride-hailing profits ever come?

TechCrunch’s favorites from Techstars’ Boston, Chicago and workforce accelerators

Image Credits: Techstars (opens in a new window)

In the theater, a “four-hander” is a play that was written for four actors.

Today, I’m appropriating the term to describe this roundup by Greg Kumparak, Natasha Mascarenhas, Alex Wilhelm and Jonathan Shieber that recaps their favorite startups from Techstars accelerators.

The quartet selected four startups each from Chicago, Boston and Techstars Workplace Development.

“As always, these are just our favorites, but don’t just take our word for it. Dig into the pitches yourself, as there’s never a bad time to check out some super-early-stage startups.”

TechCrunch’s favorites from Techstars’ Boston, Chicago and workforce accelerators

As more insurtech offerings loom, CEO Dan Preston discusses Metromile’s SPAC-led debut

Image Credits: Nigel Sussman (opens in a new window)

Neoinsurance company Metromile began trading publicly this week after it combined with a special purpose acquisition company.

Metromile will likely be one of 2021’s many SPAC-led debuts, so Alex interviewed CEO Dan Preston to learn more about the process and what he learned along the way.

A notable takeaway: “Preston said SPACs are designed for a specific class of company; namely those that want or need to share a bit more story when they go public.”

As more insurtech offerings loom, CEO Dan Preston discusses Metromile’s SPAC-led debut

Adtech and martech VCs see big opportunities in privacy and compliance

Blue Little Guy Characters Vector art illustration.Copy Space.
Image Credits: alashi (opens in a new window) / Getty Images

Senior Writer Anthony Ha and Extra Crunch Managing Editor Eric Eldon surveyed three investors who back adtech and martech startups to learn more about what they’re looking for and whether deal flow has recovered at this point in the pandemic:

  • Eric Franchi, partner, MathCapital
  • Scott Friend, partner, Bain Capital Ventures
  • Christine Tsai, CEO and founding partner, 500 Startups

3 adtech and martech VCs see major opportunities in privacy and compliance

Commercializing deep tech startups: A practical guide for founders and investors

BEIJING, CHINA - MAY 26: A researcher deals with a wafer arrayed with carbon nanotubes (CNT) at a laboratory on May 26, 2020 in Beijing, China. (Photo by VCG/VCG via Getty Images)
Image Credits: VCG (opens in a new window) / Getty Images

I have a hard time envisioning all of the hurdles deep tech founders must overcome before they can land their first paying customer.

How do you sustainably scale a company that probably doesn’t have revenue and isn’t likely to for the foreseeable future? How big is the TAM for an unproven product in a marketplace that’s still taking shape?

Vin Lingathoti, a partner at Cambridge Innovation Capital, says entrepreneurs operating in this space face a unique set of challenges when it comes to managing growth and risk.

“Often these founders with Ph.D.s and postdocs find it hard to accept their weaknesses, especially in nontechnical areas such as marketing, sales, HR, etc.,” says Lingathoti.

Commercializing deep tech startups: A practical guide for founders and investors

How will investors value Metromile and Oscar Health?

Image Credits: Nigel Sussman (opens in a new window)

This week, auto insurance startup Metromile completed its combination with SPAC INSU Acquisition Corp. II.

Last Friday, health insurance company Oscar Health announced its plans to launch an initial public offering.

As the saying goes: Past performance is no guarantee of future results, but using 2020 debuts by neoinsurance firms Lemonade and Root as a reference point, Alex says the IPO window is wide open for other players in the space.

“All the companies in our group are pretty good at adding customers to their businesses,” he found.

How will investors value Metromile and Oscar Health?

Dear Sophie: How can I improve our startup’s international recruiting?

lone figure at entrance to maze hedge that has an American flag at the center
Image Credits: Bryce Durbin/TechCrunch

Dear Sophie:

We’ve been having a tough time filling vacant engineering and other positions at our company and are planning to make a more concerted effort to recruit internationally.

Do you have suggestions for attracting workers from abroad?

— Proactive in Pacifica

Dear Sophie: How can I improve our startup’s international recruiting?

5 creator economy VCs see startup opportunities in monetization, discovery and much more

Young man sitting in a room divided by brain hemispheres.Creative half and logical half.
Image Credits: ALLVISIONN (opens in a new window) / Getty Images

The people who produce viral TikTok duets, in-demand Substack newsletters and popular YouTube channels are doing what they love. And the money is following them.

Many of these emerging stars have become media personalities with full-fledged production and distribution teams, giving rise to what one investor described as “the enterprise layer of the creator economy.”

More VCs are backing startups that help these digital creators monetize, produce, analyze and distribute content.

Natasha Mascarenhas and Alex Wilhelm interviewed five of them to learn more about the opportunities they’re tracking in 2021:

  • Benjamin Grubbs, founder, Next10 Ventures
  • Li Jin, founder, Atelier Ventures
  • Brian O’Malley, general partner, Forerunner Ventures
  • Eze Vidra, managing partner, Remagine Ventures
  • Josh Constine, principal, SignalFire

5 creator economy VCs see startup opportunities in monetization, discovery and much more

Are SAFEs obscuring today’s seed volume?

Image Credits: Nigel Sussman (opens in a new window)

Simple agreements for future equity are an increasingly popular way for startups to raise funds quickly, but “they don’t generate the same paperwork exhaust,” Alex Wilhelm noted this week.

This creates cognitive dissonance: Investors see a hot market, while people who rely on public data (like journalists) get a different picture.

“SAFEs have effectively pushed a lot of public signal regarding seed deals, and even smaller rounds, underground,” says Alex.

Are SAFEs obscuring today’s seed volume?

Container security acquisitions increase as companies accelerate shift to cloud

Data generated image of CPU in space.
Image Credits: Andriy Onufriyenko / Getty Images

Many enterprise companies were snapping up container security startups before the pandemic began, but the pace has picked up, reports Ron Miller.

The growing number of companies going cloud-native is creating security challenges; the containers that package microservices must be correctly configured and secured, which can get complicated quickly.

“The acquisitions we are seeing now are filling gaps in the portfolio of security capabilities offered by the larger companies,” says Yoav Leitersdorf, managing partner at YL Ventures.

Container security acquisitions increase as companies accelerate shift to cloud

Two $50M-ish ARR companies talk growth and plans for the coming quarters

illustration of money raining down
Image Credits: Bryce Durbin / TechCrunch

In December 2019, Alex Wilhelm began reporting on startups that had reached the $100M ARR mark. A year later, he decided to reframe his focus.

“Mostly what we managed was to collect a bucket of companies that were about to go public,” he said.

Since then, he has recalibrated his sights. In the latest entry of a new series focusing on “$50M-ish” companies, he studies SimpleNexus, which offers digital mortgage software, and photo-editing service PicsArt.

Alex has more interviews and data dives coming on other companies in this cohort, so stay tuned.

Two $50M-ish ARR companies talk growth and plans for the coming quarters

With a higher IPO valuation, is Bumble aiming for Match.com’s revenue multiple?

Image Credits: Nigel Sussman (opens in a new window)

Dating platform Bumble initially set a price of $28 to $30 for its upcoming IPO, but at its new range of $37 to $39, Alex calculated that it could reach a max valuation of $7.4 billion to $7.8 billion.

Extrapolating revenue from its Q3 2020 numbers, he attempted to find the company’s run rate to see if it’s overpriced — and how well it stacks up against rival Match.

With a higher IPO valuation, is Bumble aiming for Match.com’s revenue multiple?

Oscar Health’s IPO filing will test the venture-backed insurance model

Mario Schlosser (Oscar Health) at TechCrunch Disrupt NY 2017

Jon Shieber and Alex Wilhelm co-bylined a story about Oscar Health, which filed to go public last week.

Although the health insurance company claims 529,000 members and a compound annual growth rate of 59%, “it’s a deeply unprofitable enterprise,” they found.

Jon and Alex parsed Oscar Health’s 2019 comps and its 2020 metrics to take a closer look at the company’s performance.

“Both Oscar and the high-profile SPAC for Clover Medical will prove to be a test for the venture capital industry’s faith in their ability to disrupt traditional healthcare companies,” they write.

Oscar Health’s IPO filing will test the venture-backed insurance model

SoftBank and the late-stage venture capital J-curve

TOKYO, JAPAN - FEBRUARY 12: SoftBank Group Corp. TOKYO, JAPAN - FEBRUARY 12: SoftBank Group Corp. Chairman and Chief Executive Officer Masayoshi Son speaks during a press conference on February 12, 2020 in Tokyo, Japan. SoftBank reported its third-quarter earnings results today following the approval of a merger between T-Mobile US Inc. and SoftBank's U.S. telecom unit Sprint Corp. from a federal judge. (Photo by Tomohiro Ohsumi/Getty Images)
Image Credits: Tomohiro Ohsumi (opens in a new window) / Getty Images

Managing Editor Danny Crichton filed a column about Softbank’s Vision Fund that tried to answer a question he asked in 2017: “What does a return profile look like at such a late stage of investment?”

Softbank’s recent earnings report shows that its $680 million bet on DoorDash paid off handsomely, bringing back $9 billion. Compared to its competition, “the fund is actually doing quite decent right now,” he wrote. But Softbank has invested $66 billion in 74 unexited 74 companies that are worth $65.2 billion today.

“SoftBank quietly chopped half of the performance fees for its VC managers, from $5B to $2.5B, which led us to ask: are the best investments in the fund already in SoftBank’s rearview mirror? One upshot: WeWork seems to have turned something of a corner, with some improvements in its debt profile portending more positive news post-COVID-19.”

SoftBank and the late-stage venture capital J-curve

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Watch the Apple Intelligence reveal, and the rest of WWDC 2024 right here

Apple’s SDKs (software development kits) have been updated with a variety of new APIs and frameworks.

Apple brings its GenAI ‘Apple Intelligence’ to developers, will let Siri control apps

Older iPhones or iPhone 15 users won’t be able to use these features.

Apple Intelligence features will be available on iPhone 15 Pro and devices with M1 or newer chips

Soon, Siri will be able to tap ChatGPT for “expertise” where it might be helpful, Apple says.

Apple brings ChatGPT to its apps, including Siri

Apple Intelligence will have an understanding of who you’re talking with in a messaging conversation.

Apple debuts AI-generated … Bitmoji

To use InSight, Apple TV+ subscribers can swipe down on their remote to bring up a display with actor names and character information in real time.

Apple TV+ introduces InSight, a new feature similar to Amazon’s X-Ray, at WWDC 2024

Siri is now more natural, more relevant and more personal — and it has new look.

Apple gives Siri an AI makeover

The company has been pushing the feature as integral to all of its various operating system offerings, including iOS, macOS and the latest, VisionOS.

Apple Intelligence is the company’s new generative AI offering

In addition to all the features you can find in the Passwords menu today, there’s a new column on the left that lets you more easily navigate your password collection.

Apple is launching its own password manager app

With Smart Script, Apple says it’s making handwriting your notes even smoother and straighter.

Smart Script in iPadOS 18 will clean up your handwriting when using an Apple Pencil

iOS’ perennial tips calculating app is finally coming to the larger screen.

Calculator for iPad does the math for you

The new OS, announced at WWDC 2024, will allow users to mirror their iPhone screen directly on their Mac and even control it.

With macOS Sequoia, you can mirror your iPhone on your Mac

At Apple’s WWDC 2024, the company announced MacOS Sequoia.

Apple unveils macOS Sequoia

“Messages via Satellite,” announced at Apple’s WWDC 2024 keynote, works much like the SOS feature does.

iPhones will soon text via satellite

Apple says the new design will lead to less time searching for photos.

Apple revamps its Photos app for iOS 18

Users will be able to lock an app when they hand over their phone.

iOS 18 will let you hide and lock apps

Apple’s WWDC 2024 keynote was packed, including a number of key new updates for iOS 18. One of the more interesting additions is Tap to Cash, which is more or…

Tap to Cash lets you pay by touching iPhones

In iOS 18, Apple will now support long-requested functionality, like the ability to set app icons and widgets wherever you want.

iOS 18 will finally let you customize your icons and unlock them from the grid

As expected, this is a pivotal moment for the mobile platform as iOS 18 is going to focus on artificial intelligence.

Apple unveils iOS 18 with tons of AI-powered features

Apple today kicked off what it promised would be a packed WWDC 2024 with a handful of visionOS announcements. At the top of the list is the ability to turn…

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The security firm said the attacks targeting Snowflake customers is “ongoing,” suggesting the number of affected companies may rise.

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French startup Kelvin, which uses computer vision and machine learning to make it easier to audit homes for energy efficiency, has raised $5.1M.

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